Acetone → Dimethyl (2-oxopropyl)phosphonate

HRID 1734286Notes

Reaction equation

HRID 1734286 reaction equation
[I-].[K+].[CH3:3][C:4]([CH3:6])=[O:5].ClCC(=O)C.[CH3:12][O:13][P:14]([O:17]C)[O:15][CH3:16]>C(#N)C>[O:5]=[C:4]([CH3:6])[CH2:3][P:14](=[O:17])([O:15][CH3:16])[O:13][CH3:12]

Participants

6

Reactant 4

HCID 180AcetoneHCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 8472Trimethyl phosphite

Product 1

HCID 77872Dimethyl (2-oxopropyl)phosphonateYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A 2-liter eggplant type flask was charged with 179.2 g (1.081 mol) of potassium iodide, 300 ml of acetone and 250 ml of acetonitrile, to which 100 g (1.081 mol) of chloroacetone were added, thereby forming a white suspension. Further, 134 g (1,081 tool) of trimethylphosphite were added to stir the resulting mixture for 6 hours at 20° C. and for 4 hours at 50° C. After the thus-obtained solution was filtered through Celite, the solvent was distilled off to obtain a product in the form of a brown oil. This oily product was subjected to fractional distillation under reduced pressure (at 81-85° C. and 0.02 mmHg) to obtain 127.5 g (yield: 71%) of dimethyl 2-oxopropylphosphonate. The result of analysis of this compound by 1H-NMP is described below.

Workup

  1. additionwere added
  2. customforming a white suspension
  3. waitfor 4 hours at 50° C
  4. filtrationAfter the thus-obtained solution was filtered through Celite
  5. distillationthe solvent was distilled off
  6. customto obtain a product in the form of a brown oil
  7. distillationThis oily product was subjected to fractional distillation under reduced pressure (at 81-85° C. and 0.02 mmHg)

Sources & evidence

ORD record
ord-5133b7b93f5f4f7691db88a617aa1bb2
Source dataset
uspto-grants-1996_07
Patent number
US05532402

Reaction notes

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